Ammonium Chloride → HCID 69085942, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-4-[2-(4-fluoro-phenyl)-pyrrolidin-1-yl]-pyridine (97 mg, 0.35 mmol), tris(dibenzylideneacetone)dipalladium(0) (32 mg, 0.035 mmol) and 2-(dicyclohexylphosphino)biphenyl (25 mg, 0.070 mmol) are mixed in dry THF (2.0 mL). Then Argon is bubbled through the solution for 5 min and 1.0 M LiHMDS (0.53 mL, 0.53 mmol) is added. Then the reaction mixture is heated at 65° C. for 6 hrs before more 1.0 M LiHMDS (0.53 mL, 0.53 mmol) is added. The resulting mixture is heated at 65° C. for another 16 hrs. Then saturated NH4Cl aqueous solution (20 mL) is added along with water (25 mL). The mixture is extracted with EtOAc (3×50 mL) and the organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) followed by Gilson preparative HPLC affords 61 mg of desired product.

Provenance & Evidence